Water → 5-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid

Participants

Reaction Conditions

Reaction Steps

To 300 ml of a solvent mixture of tetrachloromethane, acetonitril and water (10:10:15) are added sequentially 8.5 g (25 mmole) of 1-fluoro-4-nitro-5-trichlorovinyl-2-trifluoromethyl-benzene, 1 g (8 mol%) of ruthenium trichloride monohydrate and 23 g (0.1 mole) of sodium periodate. After stirring at 60° C. for 16 hours additional 1 g of ruthenium trichloride monohydrate and 23 g of sodium periodate are added and stirring at 60° C. is continued for 4 hours. The cooled reaction is filtered over Celite and the filtrate evaporated to dryness. 150 ml of a 1M sodium hydroxide solution are added and extracted two times with 150 ml of dichloro-methane. The aqueous phase is acidified with concentrated hydrochloric acid and extracted four times with 100 ml dichloro-methane. The combined organic phases are dried over sodium sulfate, filtered and evaporated. The residue is recrystallized from acetone/petrolether to give 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid of m.p. 142-145° C.

Provenance & Evidence